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Insurance Transformation Jobs in Ontario (NOW HIRING)

We are seeking a Manager, Transformation Delivery to lead our low-code solution delivery team and ... Experience within Group Benefits, Insurance, or Financial Services operations. * Experience with ...

We are seeking a Manager, Transformation Delivery to lead our low-code solution delivery team and ... Experience within Group Benefits, Insurance, or Financial Services operations. * Experience with ...

Lloyd's is the world's leading insurance and reinsurance marketplace, bringing together the world ... The Tax Transformation Manager will work across all tax workstreams to drive execution of strategic ...

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Insurance Transformation information

What are some common challenges faced by professionals working in insurance transformation roles?

Professionals in Insurance Transformation often encounter challenges such as navigating legacy systems, managing resistance to change among staff, and aligning technology upgrades with regulatory requirements. These roles require strong project management and communication skills to successfully implement new digital solutions while ensuring minimal disruption to daily operations. Collaborating with cross-functional teams—including IT, compliance, and business units—is crucial for achieving seamless transitions and long-term success.

What is insurance transformation?

Insurance transformation refers to the process where insurance companies adopt new technologies, processes, and business models to improve efficiency, customer experience, and competitiveness. This often involves digitalizing operations, leveraging data analytics, and automating workflows to better meet the changing needs of customers and regulatory environments. The goal is to modernize legacy systems, streamline claims and underwriting, and create innovative insurance products. Successful transformation can help insurers stay relevant in a rapidly evolving industry and respond more quickly to market demands.

What are the key skills and qualifications needed to thrive in insurance transformation, and why are they important?

To thrive in Insurance Transformation, you need a solid understanding of insurance operations, digital transformation principles, and project management, often supported by a degree in business, IT, or related fields. Familiarity with core insurance platforms, data analytics tools, and certifications like PMP or Agile methodologies is highly valuable. Exceptional communication, change management, and stakeholder collaboration skills help drive adoption and manage organizational shifts. These capabilities are crucial for successfully leading modernization efforts and ensuring insurers remain competitive in a rapidly evolving industry.

What is the difference between Insurance Transformation vs Insurance Underwriter?

AspectInsurance TransformationInsurance Underwriter
Primary RoleLeading initiatives to modernize and optimize insurance processes, systems, and business modelsAssessing risks and determining policy terms for individual insurance applications
Required SkillsProject management, change management, industry knowledge, technical skillsRisk assessment, underwriting expertise, industry regulations, decision-making
Work EnvironmentCross-functional teams, strategic planning, often in corporate or consulting settingsUnderwriting departments, insurance companies, client-facing roles
CertificationsTypically none specific; industry knowledge and project management certifications helpfulChartered Property Casualty Underwriter (CPCU), Fellow of the Insurance Institute of America (IIA)

Insurance Transformation focuses on modernizing insurance operations through strategic initiatives, while Insurance Underwriters evaluate individual risks to determine policy terms. Both roles require industry knowledge, but their responsibilities and work environments differ significantly.

What are popular job titles related to Insurance Transformation jobs in Ontario? For Insurance Transformation jobs in Ontario, the most frequently searched job titles are:
What job categories do people searching Insurance Transformation jobs in Ontario look for? The top searched job categories for Insurance Transformation jobs in Ontario are:
Infographic showing various Insurance Transformation job openings in Ontario as of August 2026, with employment types broken down into 80% Full Time, and 20% Contract. Highlights an 100% In-person job distribution.

P&C Reserving and Capital Senior Director

Willis Towers Watson (WTW)

Toronto, ON

Full-time

Posted 9 days ago


Willis Towers Watson rating

8.3

Company rating: 8.3 out of 10

Based on 44 frontline employees who took The Breakroom Quiz

38th of 150 rated financial services


Job description

WTW is looking for a senior reserving professional with extensive Canadian P&C insurance and reinsurance experience to join the Canadian P&C Reserving and Capital Propositions of WTW's Insurance Consulting and Technology (ICT) business. In this role, you will play a leading part in a globally recognized, industry-leading consulting team, providing high value-added consulting, reserving, capital and technology insights to clients, developing and applying state-of-the-art intellectual property, and contributing to the growth of our reserving and capital practice.

About ICT

ICT provides a powerful combination of advisory services for insurance companies, integrated with leading-edge technology solutions and software, all underpinned by unparalleled analytical capability. We are a globally recognized leader in P&C insurance and reinsurance reserving, capital, financial reporting and insurance transformation, delivering robust and innovative solutions to clients across the industry facing a complex and evolving landscape.

Our goal is to continue to position reserving as a driver of value to Canadian P&C insurers through market insights, state-of-the-art analytics, process excellence, effective communication and technology-enabled delivery, and to further establish the WTW Reserving and Automation technology suite, including ResQ and Unify, as a key enabler of the modern reserving function.

The Role

As a Canada P&C Reserving Senior Director, you will lead client engagements and project teams dedicated to developing and delivering reserve, capital and reserving transformation analyses for insurance and reinsurance clients. You will play a key role in the growth of the Canadian reserving practice by leading and supporting client relationships as a senior practitioner, Client Relationship Manager and thought leader.

As an engagement and project leader, you will oversee client and project teams, serve as a senior resource to managers, consultants and analysts, and help colleagues build their technical, market-facing and client-facing expertise. You will be expected to meet revenue and billable hour goals, contribute to intellectual property and research development, and help position WTW as a leading reserving advisor in Canada.

Your main responsibilities will be:

  • Lead and support Canadian P&C reserving, capital, Appointed Actuary and reserve transformation engagements
  • Develop trusted advisor relationships with senior client contacts through effective communication and efficient, high-quality execution of projects
  • Play a visible external role in the Canadian marketplace as a senior practitioner and subject matter expert
  • Identify, pursue and support new business opportunities, including statements of work, project plans, budgets, proposals and senior client discussions
  • Contribute to and/or lead reserve transformation and process automation engagements focused on effective implementation and use of ResQ, Unify and related WTW technology
  • Manage client expectations, raise appropriate issues to Subject Matter Experts or Client Relationship Managers, and coordinate effectively across teams
  • Collaborate with colleagues in reserving, capital modelling, pricing, underwriting, claims, technology and other practices locally and globally to create, sell and deliver actuarial and technology solutions
  • Participate in the development and dissemination of thought leadership, intellectual capital and technology-enabled reserving solutions
  • Foster a strong community of reserving-focused colleagues through coaching, mentorship and technical leadership

Financials

You will contribute to a profitable and growing Canada P&C Reserving proposition.

  • Participate fully in the achievement of the Canadian reserving practice and overall ICT business plan and budget
  • Meet individual billable hour and sales targets commensurate with seniority and area of focus
  • Develop new business opportunities and enhance existing relationships that support achievement of revenue goals

Qualifications

  • FCIA with 10+ years of relevant experience in a Canadian insurance, reinsurance, actuarial or consulting environment involving reserving, capital management/modelling, IFRS 17 and/or reserve transformation

  • Deep knowledge of the Canadian P&C insurance market, including personal lines, commercial lines and reinsurance
  • Qualified and able to step into Appointed Actuary roles in Canada immediately
  • Membership in the Canadian Institute of Actuaries is required
  • Strong analytical skills, including the ability to draw conclusions and identify trends from data in a logical, systematic way
  • Proven experience successfully managing multiple complex projects and producing quality deliverables on time and within budget
  • Ability to build strong relationships and influence decision-making at senior levels
  • Self-driven, comfortable navigating ambiguity and able to develop practical, innovative solutions
  • Practiced in contributing to complex, high-profile projects and communicating technical insights to non-actuarial executive audiences
  • Strong client relationship, interpersonal and team skills, with a demonstrated ability to collaborate across functions and geographies
  • Ability to see the "big picture," leveraging the resources of related practices to address clients' broader business challenges
  • Working knowledge of Excel, Word and PowerPoint
  • Availability to travel as needed

Preferred Skills and Experiences

  • Experience in pricing, predictive analytics, stochastic reserving, capital modelling, claims analytics or actuarial transformation
  • Experience with WTW software including ResQ, Igloo, Radar/Emblem and/or Unify
  • Experience working in an actuarial consulting environment, including sales, business development and client relationship management
  • Active involvement in relevant professional or industry associations
  • Experience with multinationals, global portfolios, captives or legacy liabilities is an asset

This position is based in Canada and is open for hybrid/virtual work, subject to business needs.

Visa employment-based non-immigrant visa sponsorship and/or assistance is not offered for this specific job opportunity.

Compensation

The base salary compensation range being offered for this role is $225,000 CAD -$325,000 CAD per year.

This role is also eligible for an annual short-term incentive bonus.

Artificial Intelligence (AI) tools may be used in the process to screen, assess, or select applicants for a position but all final decisions and determinations are made exclusively by authorized human personnel.

This job posting is an advertisement for an existing vacancy.

Equal Opportunity Employer

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